One thing that you should know before buying your first (or maybe your fifth) pair of boots is that it is never attractive to wear boots when it is not the right season. In some cases a sweet pair of moccasin boots can be hot in the summer time, but wearing big, wooly boots with a mini skirt to a barbeque is never cute, no matter how many celebrities may be doing it. While we're on the topic, it is debatable whether boots with miniskirts is ever really attractive, even in winter, so keep that in mind when choosing your outfits.